4-Fluorobenzoyl chloride → 4''-[3-Butyl-5-oxo-1-(2-trifluoromethyl-phenyl)-1,5-dihydro-[1,2,4]triazol-4-ylmethyl]-biphenyl-2-sulfonic acid 4-fluoro-benzoylamide

HRID 36199

Reaction equation

HRID 36199 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[S:34](=[O:37])(=[O:36])[NH2:35])=[CH:24][CH:23]=2)[C:7](=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])[N:9]=1)[CH2:2][CH2:3][CH3:4].[F:38][C:39]1[CH:47]=[CH:46][C:42]([C:43](Cl)=[O:44])=[CH:41][CH:40]=1>>[CH2:1]([C:5]1[N:6]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[S:34](=[O:37])(=[O:36])[NH:35][C:43](=[O:44])[C:42]3[CH:46]=[CH:47][C:39]([F:38])=[CH:40][CH:41]=3)=[CH:24][CH:23]=2)[C:7](=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 103469025-n-Butyl-2,4-dihydro-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one

Product 1

HCID 100094784''-[3-Butyl-5-oxo-1-(2-trifluoromethyl-phenyl)-1,5-dihydro-[1,2,4]triazol-4-ylmethyl]-biphenyl-2-sulfonic acid 4-fluoro-benzoylamideYield 93%

Procedure

The title compound was prepared in 93% yield by reaction of 5-n-butyl-2,4-dihydro-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one (from Example 16, Step C) with 4-fluorobenzoyl chloride according to the procedure of Example 13, Step C. Column chromatography on silica gel (gradient elution with 0.5-5% MeOH in CH2Cl2) provided the material as cream-colored crystals, mp 120°-122° C.; satisfactory purity by TLC in 9:1 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 691 (M+K)+.

Sources & evidence

ORD record
ord-74b4fa3d7f444162b4fb36ce2c42d983
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Linked notes

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